1,2,5,6,9,10-Hexabromocyclododecane

Base Information

• Chemical Name: 1,2,5,6,9,10-Hexabromocyclododecane
• CAS No.: 3194-55-6
• Deprecated CAS: 23774-70-1
• Molecular Formula: C12H18Br6
• Molecular Weight: 641.699
• Hs Code.: 29038900
• European Community (EC) Number: 221-695-9
• UNII: 66OON1WWOS
• DSSTox Substance ID: DTXSID4027527
• Nikkaji Number: J4.447D
• Wikipedia: Hexabromocyclododecane
• Wikidata: Q420301
• ChEMBL ID: CHEMBL375298
• Mol file: 3194-55-6.mol

Synonyms:1,2,5,6,9,10-hexabromocyclododecane;HBCD compound;hexabromocyclododecane;hexabromocyclododecane (mixed isomers)

Chemical Property of 1,2,5,6,9,10-Hexabromocyclododecane

Chemical Property:

• Appearance/Colour: off-white to beige crystalline powder and chunks
• Vapor Pressure: 7.8E-10mmHg at 25°C
• Melting Point: 188-191 °C
• Refractive Index: 1.598
• Boiling Point: 505.2 °C at 760 mmHg
• Flash Point: 249.5 °C
• PSA: 0.00000
• Density: 2.145 g/cm³
• LogP: 6.92160
• Solubility.: acetone: soluble25mg/mL, clear, colorless to light yellow
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 641.64473
• Heavy Atom Count: 18
• Complexity: 175

Purity/Quality:

99% min ^*data from raw suppliers

1,2,5,6,9,10-Hexabromocyclododecane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-64-50/53-63
• Safety Statements: 22-24/25-61-60-36/37-53

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Other Plasticizers
• Canonical SMILES: C1CC(C(CCC(C(CCC(C1Br)Br)Br)Br)Br)Br
• Uses: 1. It can be used in smoldering, for polystyrene foamed plastics, polypropylene and polyester, acrylic, polypropylene and other fabrics as smoldering finishing agent. 2. It is mainly used for thermoplastic and thermosetting polymers which have fire retardant requirements. It is particularly suitable for extrusion of foaming polystyrene. 3. It is used for the fire-retardant polystyrene of polypropylene plastics and fibers. It can also be used for the fire retardancy of finishing and leather double-sided coat after the fire-retardancy of polyester fabric. When used as additive fire retardants, it is especially suitable for polystyrene, unsaturated polyester, polycarbonate, polypropylene, synthetic rubber or the like. 1,2,5,6,9,10-Hexabromocyclododecane(HBCD) was used to compare the efficiency of different advanced extraction techniques for the recovery of brominated flame retardants from styrenic polymers. It was used to study the kinetics of the thermal and photolytic segregation of HBCD using HPLC.
• Production method: First synthesize trans, trans, cis-cyclododecene triene (see also 10850): add butyl titanate and diethyl aluminum chloride together into benzene; further add butadiene at a temperature below 55 ℃ and make trans, trans, cis-cyclododecene-1,5,9-triene (C12H18, [2765-79-9]) through Tri-polymerization reaction. Then further obtain hexabromocyclododecane through bromination. To a 2000 L enameled pot reactor equipped with a reflux cooler and exhaust processing apparatus 2000L, add 1300 L of ethanol and 278 kg of trans, cis-ring two two-1, 5, 9-triene and 872 kg of bromine with the feed temperature being 15-25 ℃. During the entire process of adding materials, upon maintaining the presence of free bromine ion, the reaction color was red. After the reaction, remove the excess amount of bromine needle and have generated hexabromocyclododecane be subject to filtration, refinement to obtain 1000 kg of products with the yield being 91%. Another approach is applying aluminum chloride as the catalyst. To 800 parts of the Cyclododecyl-1, 5, 9-triene and 1500 parts of ethanol, add 150 parts of aluminum trichloride at 15-25 ℃m, followed by the addition of 2400 parts of bromine at 25-30 ℃ within 2h; Stir and have the reaction for 5 hour at room temperature and then filter. The filtered cake was washed by 200 parts of ethanol and 2% sodium bicarbonate to obtain hexabromocyclododecane with the yield being 86%. Moreover, the supplement of halogenated hydrocarbons to the ethanol can further inhibit the formation of resinous substance.

Technology Process of 1,2,5,6,9,10-Hexabromocyclododecane

There total 5 articles about 1,2,5,6,9,10-Hexabromocyclododecane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) → 1,2,5,6,9,10-hexabromocyclododecane (3194-55-6)

Guidance literature:

With sodium hypochlorite; hydrogen bromide; sodium sulfite; In dichloromethane; cyclohexane; water; at 0 ℃; for 0.0166667h; Flow reactor;

DOI:10.3390/molecules24112116

Reference yield: 96.0%

cyclododeca-1,5,9-triene (4904-61-4) → 1,2,5,6,9,10-hexabromocyclododecane (3194-55-6)

Guidance literature:

With bromine; In dichloromethane; 2-methyl-propan-1-ol; chloroform; at 14 - 15 ℃; pH=7; Large scale;

Reference yield: 61.0%

(1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) → 1,2,5,6,9,10-Hexabrom-cyclododecan (3194-55-6,4736-49-6,65701-47-5,134237-50-6,134237-51-7,134237-52-8,138257-17-7,138257-18-8,138257-19-9)

Guidance literature:

With bromine; In acetic acid; at 20 ℃; for 3h;

upstream raw materials:

(1E,5E,9Z)-cyclododeca-1,5,9-triene

(1E,5E,9E)-cyclododeca-1,5,9-triene

cyclododeca-1,5,9-triene

Downstream raw materials:

cis,cis,trans-1,5,9-cyclododecatriene

heptalene

Refernces

• 1、 Van Kerrebroeck, Reinout,Naert, Pieter,Heugebaert, Thomas S.A.,D’hooghe, Matthias,Stevens, Christian V.. "Electrophilic bromination in flow: A safe and sustainable alternative to the use of molecular bromine in batch". . . Retrieved 2019/06/10.
• 2、 -. "New process for producing hexabromocyclododecane". Paragraph 0024; 0025; 0027. . Retrieved 2018/09/13.